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As we inch toward the extended 2020 tax deadline of May 17, many filers are still laboring over their returns. Some are completing the final return for a loved one lost in what was a brutal year. As is human nature, most taxpayers try to squeeze every last deduction and income-reducing item into their prior-year numbers. While maximizing all available and legal tax-cutting strategies is the proper way to file a return, be aware that not all tax benefits are available to all tax filers, especially after a person has passed away.

On May 5, the House Ways and Means Committee unanimously passed the Securing a Strong Retirement Act of 2021. According to lawmakers, the proposal is designed to pick up where the SECURE Act of 2019 left off and help increase retirement savings even more. The so-called “Son of SECURE” would make more big changes to retirement accounts. Here are some highlights:

Question:I am 83 years old with an IRA rollover account, regular IRA account and a small Roth IRA. If I convert a portion of either the rollover or regular IRA to a Roth IRA and die before 5 years after the conversion, is there any penalty to me or the beneficiaries? Also, can I convert to the existing Roth IRA or should I start a new Roth IRA? I do not plan to make any withdrawals from any Roth IRA. Does it make a difference from which IRA I convert funds?Thank you for your response,George

Most of us have a pretty good understanding of how IRA and 401(k) plan benefits are taxed. But the taxation rules for defined benefit (DB) plans are less familiar, probably because there are fewer DB plans out there these days.DB plans usually offer several types of annuity distribution options, but most do not offer a lump sum distribution option. Under the tax code, only “eligible rollover distributions” can be rolled over to an IRA or another company plan. Annuity payments do not qualify (unless payments are scheduled over a period of fewer than ten years). So, benefits payable from DB plans are typically fully taxable in the year received and cannot be rolled over.

When visiting the doctor, does he or she ask foundational questions to help determine your medical condition? Of course. “How are you feeling?” “Are you a smoker?” “What hurts?” Does the doctor take some basic measurements – height, weight, blood pressure? Does he listen to your heart and lungs? Most assuredly.The doctor is establishing an overall picture of health so as to make informed medical decisions. Without such elemental knowledge, how could a proper diagnosis be made? How could “next steps” be recommended with any confidence? It is not possible to provide appropriate care or guidance simply by looking at a person. Assumptions could be a death sentence.

Question:I was wondering if, after a person leaves employment and they are sent a required minimum distribution (RMD) from their plan (sent as a check, taxes withheld), would it be considered a rollover if the ex-employee wants to open up an IRA on her own to put the money in within the 60-day timeline to avoid the taxes?Thank youSteve

If you sponsor a solo 401(k) plan, beware!The IRS recently announced that it is targeting several employer plan areas for stepped-up auditing. One of those areas is solo 401(k) plans.The fact that solo plans made the list is a signal that the IRS believes there are widespread compliance issues with these plans. While solo 401(k) plans don’t have as many rules to follow as employer-based 401(k) plans, there are still several requirements. The IRS announcement should be a warning to business owners with solo plans to make sure they are obeying those rules.

Question:Your newsletter is so helpful, and your book was a great resource to me when my mom passed away 5 years ago and I inherited her IRA.I am 76 and have not taken my RMD for 2021. Should I pass away and my wife age 69 transfers my IRA to hers, must my RMD for 2021 be taken first?Thanks much. A columnist in the Chicago Tribune led me to you years ago.F. Perry

Question:A new customer came to me asking for help with an IRA. Unfortunately, he had already accepted a check from the 401(k) plan made out to him personally. He sat on the check for 5 months and deposited it into his checking account last week. He is only 50 years old. Since we are well after the normal 60-day rollover period, is there any way that this can be repaired? Perhaps under the CARES act of 2020 if his departure was Covid related?Any direction you can provide would be appreciated.

Just a few weeks after the start of the baseball season, the IRS has thrown us a curveball by apparently interpreting the SECURE Act 10-year payout rule in a totally-unexpected way.We say “apparently” because the IRS explanation isn’t very clear. And even if it was clear, the IRS offered the information in an informal publication that should not be relied on.Here’s the backstory: One of the major changes made by the 2019 SECURE Act was the elimination of the stretch for many beneficiaries of inherited IRAs.